SR60x

because difference of "generally" accepted good performance is right at the $200-300 level. The exceptions are known... The pair of FIIO FT1 and FT1 Pro, Philips SHP9600, Koss's 4 on ear "headphones", Grado SR60x, Sennheiser x Drop HD6xx (sale price) or even the HD58x...🤷🏻‍♂️ There's a reason why IEM is competitive with headphones at that under $300 price point. Price to performance...IEM usually perform better than headphones

Grado SR60X They pretty much cured my Gear Acquisition Syndrome. If you can get cans that sound that great for so little money, what is the point of chasing perfection?

as another glasses user I've had some offer surprisingly good comfort. Normally on-ears are a bad idea, but my grado sr60x are super comfortable *after I stretched out the headband*, you have to really stretch it out so that it applies almost no pressure to the ears, it's basically floating there, suspended only by the headband. Another is koss KSC75, again, usually having more stuff hooking to the ear is a bad idea, but I can wear these things all day long (which I have done before...). Sennheiser HD600 I was also expecting to suck, especially when I first put them on and felt how much pressure they apply. I still need to bend them a little more to relieve pressure, but even before stretching they applied more pressure near the jaw below the ear than my glasses frame. worth noting I have metal frames with wide (more like tall) but thin (1mm or less) temples, so I can get away with more pressure than frames with thick temples.

First of all, i don't think that your experience will be any better with a headphone that has a usb-c connector, since they will have the same exact type of DAC as the external ones. But you should try out the usb-C adapter by Apple. It's only 10 dollars and i have heard that it sounds just as good as audiophile adapters that cost 10 times as much. There are open back over ear headphones. I mainly use them indoors, since, i want to have as little noise as possible creeping in. When they are not playing any music, it almost feels like you are not wearing any headphones. But if you are hell bent on ear headphones, here are a few recommendations: My first pick would be Grado. They make on ear headphones that look super cool and have a very unique sound that is loved by many people. Their entry level 60x apparently sound almost identical to the more expensive 80x and 125x, so that would be a great option for the money (around 99 dollars). Then there are the Koss Porta Pro. They are one of the most legendary headphones and have received high praise for decades. They are pretty affordable at around 50 dollars (you can find them cheaper) and apparently sound pretty great for the money. The styling is a bit polarizing though, even if it is iconic.

I’d be willing to be at least half of those who dog on Grados in here have never listened to a pair. Grado sr60xs are $100. Less if on sale (which they often are). The only reason these people don’t touch Grado is a stranger on the internet made fun of them. I’m actually not a fan of Grado—they sound great but I hate the way they fit—but I at least own a pair and am speaking from experience. Buy what you want. This sub tends to be very meme-y in its suggestions.